Nitro toluylic aldehyde.



UNTTnn STATES PATENT Omen.

JOSEPH KOETSOl-IE'I, on Si. FONS, FRANCE, ASSIGNOR 'IO LA socIETE OHIMIQUE DEs USINES DU RHoN'E, ANOIENNEMENT GILLIAHD, P. MONNE'I E'l CARTIER, OF LYONS, FRANCE.

NITR'O TOL UYL|G ALDEHYDE.

SPECIFICATION forming part of Letters Patent No. 662,074, dated November 20, 1900.

Original application filed June 3, 1899, o'erial No. 719,298. Divided and this application filed June 6, 1900. Serial No. 19|l98i (No specimens.)

T0 at whom it may concern.-

Be it known that I, JOSEPH KoETsoHET, chemist,of St. Fons, near Lyons, France,have invented certain new and useful Improvements in the Manufacture of a New Nitro Compound of Toluylic Aldehyde, of which the following is a specification.

This invention has reference to the manufacture of a new nitro compound of toluylic aldehyde particularly applicable for use in the manufacture of indigo coloring-matters and intermediate products, more especially in the manner described in my application for patent dated June 3, 1899, Serial No.-

I have discovered that when meta-toluylic aldehyde is nitrated a mixture of nitro products is obtained, varying in proportion according to the conditions of nitration, and from this mixture I have isolated the crystalline mono-nitro toluylic aldehyde, hereinafter more fully described.

In carrying the present invention into effect I preferably proceed under the following conditions of nitration; but it will be understood that these conditions and the proportions of the various reagents may be varied: Two kilos of metatoluylic aldehyde are dissolved in twenty kilos concentrated sulfuric acid (ninety-eight per cent.) at a temperature of about 40 centigrade, and to this solution is added, with constant stirring, 144 kilos dry nitrate of soda. The temperature is maintained at 40 to Centigrade, and when the reaction is finished the nitrated mixture is poured upon ice. The oily mixture of nitro-aldehyde is separated by decantation, washed with water, a small quantity of nitro toluylic acid which is formed is removed by carbonate of soda, and the product again washed with water. About two and one-half kilos crude nitro-aldehyde may th us be obtained. The crude nitration product is then fractionally distilled in cacao and at a pressure of two millimeters nearly the Whole distils over between 135 and 145 centigrade. The first two-thirds of the distillate may be collected apart and treated in the manner described in another application of even date herewith for the purpose of obtaining the nitro compound therein described. The last third of the distillate is collected apart and cooled to 0 centigrade, when a crystalline mass of a nitro-aldehyde is formed and re moved from the mother-liquor by filtration at 0 centigrade. This new nitro-aldehyde crystallizes in yellow needles which when pure melt at 43 to 44 centigrade, (uncor= rected.) The mother-liquor from the filtration may be resubmitted to fractional distil- 6o lation until no further crystals are obtained from the fractions, even at a temperature of 10 centigrade. The nitro-aldehydes probably contained in the residue have not hitherto been obtained crystalline.

The method of separation from the crude nitrated tolnylic aldehyde of the crystalline product melting at 43 to 44 centigrade is merely given as typical and may be modified in detail as the proportions of this nitro prodnot in the crude material may require.

The difference between the crystalline nitro toluylic aldehyde melting at 43 to 44 centigrade and that described in my said application of even date herewith is further demonstrated by the different compounds which said nitro-aldehydes yield with anilin, hydroxylamin, phenyl-hydrazin, &c., all of which have been prepared by me. The compound of the present nitro-aldehyde with So anilin melts about 51 centigrade, the compound with hydroxylalnin melts about 105 centigrade, and the compound with phenylhydrazin about 142 centigrade. Moreover, whereas the nitro-aldehyde melting at 43 to 44 centigrade yields an unknown acid melting at 135 centigrade, the nitro-aldehyde melting at 64 centigrade yields on gentle oxidation a corresponding acid melting at 218 to 220 centigrade. o

lVhat I claim, and desire to secure by Letters Patent, is

1. As a new product nitro-toluylic aldehyde which is a derivative of meta-toluylic aldehyde and which when pure crystallizes in yellow needles melting at about 4310 44 centigrade (uncorrected) and forms a crystalline compound with anilin melting at about 51 centigrade, a crystalline compound with bydroxylamin melting at about 105 centigrade, and a crystalline compound with phenylhy- (lrazin melting at about 142 centigrade.

2. As a new product solid o-nitro-toluylic aldehyde having the methylgroup in the meta (1:3) position relatively to the aldehydic group which crystallizes in yellow needles and when pure melts at about 43 to 44 centigrade (uncorrected) and forms a crystalline compound with anilin melting at about 51 centigrade, a crystalline compound with by droxylamin melting at about 105 cent-igrade, and a crystalline compound with phenylhydrazin melting at about 142 centigrade.

In witness whereof Ihave hereunto signed my name in the presence of two subscribing witnesses. u

JOSEPH KOETSCHET.

Witnesses:

RODOLPHE PFISTER, EMIL MARQUETANT. 

